You don't wear something to work designed to taunt every customer and potential buyer that comes in that day. It was perfectly reasonable for the boss to order it removed. When the guy refused, well....

I think the guy probably meant it as a funny conversation starter. Most grown-ups buying a car realize that people have different sports loyalties, particularly when the two teams share a state border near the city.

The story I read said that he thought his boss was joking when he told him to take it off or he was going to be fired.

First time is "Oh, I thought you were kidding." Beyond that is insubordination.

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But if my boss was a Bears fan and I wore a Packers tie and he said to take it off, I could just as easily say I meet the dress code. HR would have to deal with it there. He wouldn't be able to fire me.